Distinguishing rotamers in N-trifluoroacetyl-3-benzazepine derivatives

Williams A Acevedo-Fuentes; Bruce K Cassels

doi:10.1002/mrc.4406

Distinguishing rotamers in N-trifluoroacetyl-3-benzazepine derivatives

Magn Reson Chem. 2016 Jul;54(7):597-600. doi: 10.1002/mrc.4406. Epub 2016 Jan 13.

Authors

Williams A Acevedo-Fuentes¹, Bruce K Cassels¹

Affiliation

¹ Department of Chemistry, Faculty of Sciences, University of Chile, Santiago, Chile.

PMID: 26763071
DOI: 10.1002/mrc.4406

Abstract

This paper provides the full (13) C NMR assignments for the trifluoroacetamides of five potentially appetite-reducing 5-HT2C benzazepine receptor agonists and two open-ring synthetic precursors. These compounds exist in solution as mixtures of two rotamers for each of which the (13) C NMR signals have now been assigned with the assistance of 2D NMR experiments and the carbonyl-induced shifts of the neighboring (13) CH2 resonances and long-range (13) C/(19) F couplings.

MeSH terms

Appetite Depressants / chemistry*
Benzazepines / chemistry*
Carbon Isotopes
Carbon-13 Magnetic Resonance Spectroscopy
Fluorine / chemistry
Isomerism
Oxidation-Reduction
Receptors, Serotonin / metabolism*
Serotonin Receptor Agonists / chemistry*
Thermodynamics

Substances

Appetite Depressants
Benzazepines
Carbon Isotopes
Receptors, Serotonin
Serotonin Receptor Agonists
serotonin 5 receptor
Fluorine